For the first time, four series of new phthalide-containing heteroaromatic compounds were separated by reverse phase HPLC: O_YO, O_YS, S_YS; O_YO_YO, O_YO_YS, S_YO_YS; S_YS_YS, S_YS_YO, O_YS_YO; O_YYO, O_YYS, S_YYS, (where O – diphenyloxide, S – diphenylsulfide, Y – phthalide group). A fundamental difference was established in the chromatographic behavior of diaryl(arylene)diphthalides, built on the principle of “head-to-tail”, and diaryldiphthalides with a structure of “head-to-head”. The meso and chiral diastereoisomers of the former were eluted by one peak, while the latter existed in solution in the forms of stable cis (racemic form) and trans (meso form) rotamers with different retention times. It was shown that to calculate the retention times of related diarylphthalides, diaryl(arylene)phthalides, diastereoisomeric and enantiomeric diaryldiphthalides of an asymmetric structure, the half-sum rule can be applied according to which: t_R(A-X-B)≈[(t_R(A-X-A)+t_R(B-X-B)]/2. For diaryl(arylene) diphthalides of a triadic structure, a modified additive scheme for calculating retention times is proposed, including multiplication and division operations: t_R(A-A-A) = t_R(A-A-B) × t_R(A-B-B)/t_R(B-B-B).

首次通过反相HPLC分离了四个系列的新的含邻苯二甲酸酯的杂芳族化合物：O _Y O，O _Y S，S _Y S；O O _Y O _Y O，O _Y O _Y S，S _Y O _Y S; S _Y S _Y S，S _Y S _Y O，O _Y S _Y O；O _YY O，O _YY S，S _YY S，（其中O –二苯醚，S –二苯硫醚，Y–邻苯二甲酸酯基）。建立在“首尾相接”原理基础上的二芳基（亚芳基）二邻苯二甲酸酯与“头对头”结构的二芳基二邻苯二甲酸酯的色谱行为之间存在根本差异。前者的内消旋和手性非对映异构体被一个峰洗脱，而后者以稳定的顺式（外消旋形式）和反式（内消旋形式）旋转异构体形式存在，并具有不同的保留时间。结果表明，要计算相关的二芳基邻苯二甲酸酯，二芳基（亚芳基）邻苯二甲酸酯，非对映异构体和对映体二芳基二邻苯二甲酸二苯酯具有不对称结构的保留时间，可以应用半总法则，根据其：t _R（AXB）≈[（t _R（AXA）+ t _R（（BXB）] / 2。对于三元结构的二芳基（亚芳基）二邻苯二甲酸酯，提出了一种计算保留时间的改进加法方案，包括乘法和除法运算：t _R（AAA）= t _R（AAB）×t _R（ABB）/ t _R（BBB ）。